Diisopropylamine → HCID 18436275, compound

HRID 351310Notes

Reaction equation

HRID 351310 reaction equation
I[C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[CH3:10][Si:11]([C:14]#[CH:15])([CH3:13])[CH3:12].C(NC(C)C)(C)C>C1COCC1.CCOCC.[Cu](I)I>[CH3:10][Si:11]([CH3:13])([CH3:12])[C:14]#[C:15][C:2]#[C:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9]

Participants

7

Reactant 3

HCID 7912DiisopropylamineHCID 66111TrimethylsilylacetyleneHCID 14942043HCID 14942043, compound

Product 1

HCID 18436275HCID 18436275, compoundYield 57.1%

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-iodo-6-heptynol (100 mg, 0.42 mmol), trimethylsilylacetylene (0.072 ml, 0.5 mmol), diphenyldichloropaladium (10 mg) and copper iodide (3 mg) in 5 ml of THF was added diisopropylamine (0.150 ml) at rt in argon atmosphere. After stirring 1 hr at rt, the mixture was diluted with ether, washed with NH4Cl solution, water and brine, dried over MgSO4 and concentrated. Purification by silica gel chromatography (hexanes:ethyl acetate=4:1) gave 50 mg of product (50% yield).

Workup

  1. washwashed with NH4Cl solution, water and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customPurification by silica gel chromatography (hexanes:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-3bba46fd58c44398a2227499e4b8248e
Source dataset
uspto-grants-2007_02
Patent number
US07183432B2

Reaction notes

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